1,1-Dibromoethane → 2-Hydroxy-2-adamantylethyl Vinyl Ether

HRID 22623

반응식

HRID 22623 반응식
[Mg].BrC(Br)C.[CH:6]([O:8][CH2:9][CH2:10]CCl)=[CH2:7].[CH:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[C:14]1=[O:23])[CH2:20]2>O.OS(O)(=O)=O.C1COCC1>[CH:6]([O:8][CH2:9][CH2:10][C:14]1([OH:23])[CH:15]2[CH2:21][CH:19]3[CH2:18][CH:17]([CH2:22][CH:13]1[CH2:20]3)[CH2:16]2)=[CH2:7]

참가 물질

8

반응물 4

HCID 112011,1-DibromoethaneHCID 64151AdamantanoneHCID 5462224MagnesiumHCID 221862153-Chloropropyl vinyl ether

생성물 1

HCID 865900622-Hydroxy-2-adamantylethyl Vinyl Ether

시약·촉매·용매 3

HCID 962Water용매HCID 1118Sulfuric Acid용매HCID 8028Tetrahydrofuran용매4회

실험 절차

(Step-2) Magnesium metal(2.6 g) and anhydrous tetrahydrofuran (hereinafter referred to as THF(100 mL)) were added to a round bottom flask. Next, after dripping a small quantity of dibromoethane into the round bottom flask containing the resulting mixture to promote the reaction, 3-chloropropyl vinyl ether (12 g, 0.1 mol) and anhydrous THF(100 mL) were added drop-wise thereto. Then, the mixture was reacted for 2 hours. After dripping an adequate quantity of THF containing 2-adamantanone (15 g, 0.1 mol) in the mixture, the resulting mixture was refluxed for 12 hours. After the reaction was completed, the reaction mixture was slowly dissolved in excessive water and neutralized with thin H2SO4 solution. Then, the organic layer was extracted from the reaction solution using an adequate quantity of diethyl ether and then dried with anhydrous sodium sulfate. Next, after evaporating the solvent to obtain an oily residue using a rotary evaporator, the product was separated using a column chromatography method (hexane:ethyl acetate=3:1). (Yield: 60%)

후처리

  1. additionwere added to a round bottom flask
  2. additioncontaining the resulting mixture
  3. additionwere added drop-wise
  4. customThen, the mixture was reacted for 2 hours
  5. temperaturethe resulting mixture was refluxed for 12 hours
  6. extractionThen, the organic layer was extracted from the reaction solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. customNext, after evaporating the solvent
  9. customto obtain an oily residue
  10. customa rotary evaporator
  11. customthe product was separated

출처 및 근거

ORD 기록
ord-8ba09fd2cc7646759768ea7fc99b2cf3
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849378B2

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